Ammonia → HCID 14500967, compound

HRID 620669Notes

Reaction equation

HRID 620669 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=1.C([Li])CCC.[S:18](Cl)(Cl)(=[O:20])=[O:19].[NH3:23]>CCOCC.CCCCCC>[C:7]1([C:3]2[S:4][CH:5]=[CH:6][C:2]=2[S:18]([NH2:23])(=[O:20])=[O:19])[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 24648Sulfuryl chlorideHCID 13122710HCID 13122710, compoundHCID 178418339Butyllithium

Product 1

HCID 14500967HCID 14500967, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3-bromo-2-(1-cyclohexenyl)-thiophene (prepared by the method of N. Gjos and S. Gronowitz, Acta. Chem. Scan., 26, 1851-59, (1972)) (8.0 g, 32.9 mmol) in ether (30 ml) was added dropwise to a stirring solution of n-butyllithium (1.37M, 25.2 ml, 34.6 mmol) in ether (60 ml) precooled to -78° C. The solution was stirred another 30 minutes at -78° C. and was then treated with sulfuryl chloride (3.2 ml, 40 mmol) in hexane (10 ml). After an additional 30 minutes at -78° C., anhydrous ammonia (9 ml, 300 mmol) was added, the suspension warmed to 25° C. and poured into ether, washed with water and brine, dried over magnesium sulfate and reduced in volume. The product was crystallized by trituration with butyl chloride and hexane affording 2.51 g white solid (31%) m.p. 115°-121° C.

Workup

  1. customprecooled to -78° C
  2. waitAfter an additional 30 minutes at -78° C.
  3. temperaturethe suspension warmed to 25° C.
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe product was crystallized by trituration with butyl chloride and hexane affording 2.51 g white solid (31%) m.p. 115°-121° C.

Sources & evidence

ORD record
ord-4534be0af5b44444b3db7b250b79c265
Source dataset
uspto-grants-1989_04
Patent number
US04822403

Reaction notes

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